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A couple sit on a sand dune between two palm trees, watching the sunset
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Like most people, my plans were disrupted by the pandemic.

In that narrow window of 2020 before the pandemic, I managed to visit West Virginia. But it wasn’t until this spring on my sabbatical that I finally managed to reach Hawaii.

Wanting to make the most of my one week in The Aloha State, I did a lot of online research and consulted with veterans of the islands, be they friends, family, co-workers, or clients. Having done that work, let me save you the effort: if you’re planning your own trip to Hawaii, here’s an outline of activities I found enjoyable — or not!

Which island?

Before you go to Hawaii, you need to choose an island. There are eight main islands (and 129 small islands!), and although day trips among them are possible, flights can be expensive and rarely arrive in time for a scheduled morning activity. Here are the four islands you should consider focusing on:

  • Oahu is the most populated island and host to the capital city, Honolulu. Most flights land here, and the island has a big-city feel with lots of hotels, amenities, highways, and traffic.
  • Kauaʻi is also known as “the Garden Island”, as it is relatively remote, with plenty of peace and quiet.
  • Big Island is home to two active volcanoes, Kilauea and Mauna Loa, which has resulted in some harsh landscapes.
  • Maui is the perfect blend of the above three: tons of beaches, diverse attractions and natural features, and easy access to everything without feeling too crowded.

You’d be correct in guessing I chose Maui! I stayed in south Maui in the town of Kihei, just 18 minutes south of the airport and one block from the beach. I stayed in a private room in a shared Airbnb and rented a car from Allsave for four of the seven days I was there.

Haleakalā bike tour

Since I was flying from the continental United States, I was advised to spend my first full day on Maui watching the sunrise over the dormant volcano of Haleakalā: the shuttle picked me up at 2:45 AM, but since I was still jetlagged, it felt like a more reasonable 8:45 AM. We got dropped off in Haleakalā National Park around 5:30 AM, easily in time for the 6:19 AM sunrise. As warm as Hawaii is, it was cold at that hour and altitude; I’d brought layers but wish I’d had even more for that final pre-dawn hour. Fortunately, the view was worth it.

Selfie of Ken as the sun rises over a volcano
Goooooood morning, Hawaii!

Afterward, we mounted bikes and rode 7 miles down the mountain… then got in a shuttle, went up, and rode those same 7 miles again. Our bikes were of the slower, hybrid variety (a cross between road and mountain bikes), whereas I’m accustomed to faster, sleeker road bikes. And since it was all downhill, no pedaling was involved — just some light steering. I’m sure this part of the morning would be a blast for most people, but it didn’t get my blood pumping. My understanding was that only a limited number of people are allowed into the park at sunrise, though, so that part of the package was still worth it. Still, I wish I’d made time in my itinerary to rent a road bike and tool around Maui on my own time and pace.

Ken flashing a peace sign while standing behind a hybrid bike
Volcanoes, all the way down

Road to Hana

Hana is a remote town on the eastern shore of Maui. Although not itself much of a tourist destination, the winding road to it is a wonderful, scenic loop with dozens of potential stops, resulting in a twelve-hour day trip from when the van picked me up at my Airbnb to the moment it dropped me off. Given the winding and, at times, precarious nature of the road, a guided tour is vastly preferable to a self-guided experience.

We skipped Charles Lindbergh’s grave, which I was quite okay with. But we did stop for banana bread, coconut (both the food and the beverage), honey, hiking, swimming on a black-sand beach, cliff-diving, and more. It was a long, wonderful day with plenty of variety, suitable for all age and activity levels.

The only strange part was that the booking website has a minimum party size of two; I had to call and ask for an exception to be made before my reservation was accepted. The upshot is that the van’s bench seats were reserved for those who wanted to sit together, enabling me to ride shotgun and get the best views of everything.

Kalepolepo Fishpond

This place was not initially on my radar, but when my Airbnb proprietor’s mom found out I love animals, she recommended I walk a mile up the road to Kalepolepo Fishpond. Every night at sunset, giant turtles make their way to this protected bay; when the tide is out, it’s easy to spot their enormous shells. Since they’re wild creatures, guides are on hand to ensure the turtles aren’t approached, touched, or harassed — but if a turtle happened to come to me, then that was fine.

Although possibly not worth planning an evening around, it was a neat way to spend a sunset. And the walk back to the Airbnb along the beach gave me another opportunity to encounter some beached turtles in the wild.

A large turtle surfaces in a shallow pond
I like turtles

Kayak tour

When I worked at MIT, I would often take my lunch break in a rented kayak on the Charles River. Kayaking in the ocean is something I’ve less experience with, so I leapt at the chance to hit the Hawaiian water. Most of the whale-watching kayak tours had ended for the season on March 31, so I signed up for a more general tour.

I misunderstood it to be a group tour, though, and was surprised to find I’d have a guide all to myself. Rather than having a planned itinerary, she asked me, “Where do you want to go?”, to which I could offer only a noncommittal shrug — I didn’t expect to have to do that work. I would’ve been happier (and likely faster) on my own — but when the waves grew choppy, I guess there needed to be someone more experienced to tell me to return to shore, an hour sooner than the tour was planned for. (A discount on a second tour was offered, but no partial refund on the first tour or the optional photo package.)

Ken in a kayak on the ocean
Row, row, row your boat…

Maui Gold pineapple tour

When you think of pineapples, the brand you likely think of is Dole — yet they ceased operations in Hawaii years ago. The favored brand here is instead Maui Gold, and they offer a tour of their plantation. It’s a short shuttle ride around a field of pineapples, with plenty of history, information, and free samples for those who want to take it all in. Best of all, every tourist goes home with a pineapple!

Ken biting a piece of pineapple on a toothpick
Golden delicious

Dinner cruise

This was the only experience I could’ve skipped entirely. When I checked in at the pier, I was told they had a full boat that evening, and I’d likely be seated with someone else. Great! I’m friendly! I love meeting new people!

When I boarded, I walked up and down the rows of tables, each with an assigned name and the appropriate number of place settings, looking for my new friends. It wasn’t until I got to the end of the final row that I found my seat: a table for one.

A table setting for one
One is the AWESOMEST number

I’m not the least bit hesitant or self-conscious about traveling solo, setting my own agenda, and enjoying my own company. But this dinner cruise was clearly aimed at families and couples, and sitting by myself with a mediocre vegetarian dinner was not worth the price of admission.

However, the dinner cruise inexplicably came with a coupon for a free…

Whale-watching excursion

Even though whale-watching is a service offered in my own backyard of Boston, Massachusetts, it seemed more exotic to do so in Hawaii. I was warned there may not be many whales to see at this time of year — so I was surprised and thrilled to see several mother whales and their calves! The sightings were more subtle than Free Willy-type full-body jumping out of the ocean, but to see even a fin or blowhole was more than I expected. One of our tour guides made a regular practice of “speaking Whale” (as Dory did in Finding Nemo), and I was shocked when it seemingly worked, with one whale swimming right up to the boat!

A spout of water from a whale
Whale? Or dolphin? You be the judge

Both the dinner and whale-watching cruises departed from Lahaina, a hip, walkable town about 40 minutes northwest of my Airbnb in Kihei. It’s worth visiting Lahaina for an afternoon or evening, even if you don’t have any activities booked.

Waterfall rappelling

Rappelling was by far the best experience I had on Maui. The location is along the Road to Hana, which means a precarious drive, but it was worth it.

Abbie and Shauna were my friendly, confident guides who led me and another tourist through the forest and down several cliff faces alongside natural waterfalls.

Three women and Ken pose for a selfie
There’s no repelling a good time here!

I’m only half-joking when I say I don’t have a fear of heights; I have a fear of falling. And since I was always clipped in, I knew that, even if I simultaneously lost all foot- and handholds, the worst that could happen is I’d slip only a foot or two before coming to a safe and complete stop. And with one instructor at the top of the falls and another at the bottom, I knew any question or issue I might have would be swiftly addressed.

Fortunately, the worst problem I had was trouble modulating my speed (I often went slower than I’d like). It was such a safe and fun experience that any increase in my heart rate stemmed from physical exertion only and not from concern for my wellbeing.


There were two museums I wanted to visit but didn’t get to: the Maui Historical Society Museum, which is open until 1 PM only and requires an appointment; and the Alexander & Baldwin Sugar Museum, which is open until 2 PM. I hadn’t heeded their hours and thought I could visit them after a morning whale-watch; a better planner would’ve hit up the museums first thing in the morning, then moved onto an afternoon activity.

I sincerely thought I’d be bored in Hawaii, and that my active soul would have too many lazy days at the beach. I could not have been more wrong: with a bit of research and planning, there was rarely a dull moment. Not only that, but the weather was perfect, and the people were friendly.

It’s like my Lyft driver said when I asked him how his day was going: “I have two things going for me — I woke up, and I’m in Maui. Everything else is a bonus.”

Have you been to Hawaii? What experiences would you recommend? Leave a comment with your suggestions!

Ken Gagne

Digital nomad, Apple II geek, vegetarian, teacher, cyclist, feminist, Automattician.

2 Replies to “A tourist’s guide to Maui”

  1. Haleakalā bike tour:

    As warm as Hawaii is, it was cold at that hour and altitude;
    I’d brought layers but wish I’d had even more for that final
    pre-dawn hour. Fortunately, the view was worth it.

    🙂 We found the same thing when we went on the sunSET tour. By the time the sun had set, my teeth were chattering, but the view was worth it.

    We were on a Cruise around the islands, and I really regretted not having more time to spend in Maui. If we ever go back, that will be our destination, for sure.

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